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Singlet oxygen oxidation of pyrroles. Formation of 5-substituted derivatives

✍ Scribed by Harry H. Wasserman; Mingde Xia; Jianji Wang; Anders K. Petersen; Michael Jorgensen

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
206 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

The ten-butyl ester of 3-methoxy-2-pyrrolecarboxylic acid 3 undergoes reaction with singlet oxygen to form an intermediate imino hydroperoxide 4. This hydroperoxide may be trapped by a variety of nucleophiles yielding 5substituted pyrroles 6. With strong nucleophilic substituents at the 5-position, these pyrroles may add to unreacted hydroperoxide 4 to form bipyrrole-like products 7.

πŸ“œ SIMILAR VOLUMES

Synthesis of 2,3,5-substituted pyrrole d
Synthesis of 2,3,5-substituted pyrrole derivatives
✍ Paula M.T. Ferreira; HernΓ’ni L.S. Maia; Luı́s S. Monteiro πŸ“‚ Article πŸ“… 2002 πŸ› Elsevier Science 🌐 French βš– 147 KB

Substituted pyrrole derivatives are prepared by treatment of 2,3-dihydrofuran derivatives with trifluoroacetic acid. These in turn are obtained by Michael addition of carbon nucleophiles of the b-dicarbonyl type to N-(4-toluenesulfonyl)-N-(tertbutyloxycarbonyl)-dehydroalanine methyl ester.